Blake Lively and Penn Badgley in the original 'Gossip Girl'
Cw Network/Kobal/Shutterstock


All The Messy Love Triangles From ‘Gossip Girl’

All hail the Vanessa, Dan, and Hilary Duff threesome!

Originally Published: 

Gossip Girl has gifted us with an endless number of absurd plotlines, like when Serena thinks she kills someone or when Dan and Georgina almost have a baby. Turns out that in addition to rabid chaos, Gossip Girl’s writers are also big fans of the triangle shape, putting together a seemingly endless combination of romances that include every possible character combination. Similar to how the contact lists of characters in TV shows include only the other characters in the show, there are only so many romances to milk between less than a dozen characters. Here, we break down the wildest and most persistent love triangles that dominate and define Gossip Girl.

Rufus, Lily, and Bart

The best teen dramas usually offer some eye candy for parents watching with their kids — and Rufus Humphrey was made for moms across America to lust after his hemp necklaces and the rolled-up sleeves of his flannel. Which is why it’s perplexing that Lily would continue to go back to Bass, who was maybe hot when he was guest-starring on Sex And The City, but proves again and again to be cartoon villain-level evil, especially after he tries to kill his own son! But he’s rich, and for all Lily likes to talk big game about using her trust fund to hang out backstage with Sonic Youth, all she really wants is a big, fat Cartier ring.


Dan, Blair, Chuck, and Louis (sort of)

Coupling Dan and Blair was the first but certainly not the last time Gossip Girl jumped the shark. They tried to play it off like they were intellectually connected, having them watch horror movies together or go to book readings, even though no two characters are more diametrically opposed. Even Prince Louis gets dragged into this love rhombus, when Dan writes his vows for him when he marries Blair. Chuck just waits in the wings until she goes back to him, because of course she does!

The CW

Dan, Vanessa, and Hilary Duff

Dan dates Olivia, a teen actor famous for starring in sexy vampire movies because this is the Twilight era, who is played by Hilary Duff in a deeply satisfying cameo I think about probably once a week. On her last night before leaving NYU to star in a movie, Dan, Vanessa, and Olivia have a threesome where Dan realizes he loves Vanessa. Dan and Olivia’s relationship implodes because they broke the cardinal rule of threesomes: not including your hot best friend!


Blair, Serena, and Nate

The G.O.A.T. love triangle that started the entire show: Serena hooks up with Nate at a wedding, a blurry scene we’re shown constantly throughout the show, a cinematographic choice that echoes the bleary, drunken state of Serena and Nate during the act. While Serena ultimately did Blair a favor — she and Nate didn’t need to get engaged at age, like, 16 — it’s still pretty messed up to hook up with your best friend’s boyfriend, Serena!

Sara Jaye/Shutterstock

Nate, Blair, and Chuck

After finding out about Serena and Nate hooking up, Blair — in her most iconic performance of the series — does burlesque at Chuck’s club and then has sex for the first time in the back of his limo. Nate can’t deal, even though he cheated on her with Serena, and every season or so, he falls back in love with Blair, to cause further mayhem.


Jenny, Chuck, and Blair

Blair “banishes” Jenny from the city of New York — inconvenient for someone who wants to work in fashion! — after she loses her virginity to Chuck in a moment of profound self-hatred. After Blair sabotages Jenny’s interview with Tim Gunn to attend Parsons (this writer’s room...), Jenny gets revenge by telling Gossip Girl that she and Chuck hooked up, a final mic drop before she leaves for good.


Vanessa, Jenny, and Nate

For some reason, the Brooklyn babes love Nate, a profoundly boring character with no hobbies except running around Central Park and reaping the benefits of nepotism. Vanessa and Jenny both crush on him, despite Dan telling Nate to back off because Jenny is too young for him. There’s also an instance where Nate tries to reach Jenny through a letter which Vanessa finds and destroys. I have a hard time believing either of them really liked him, but there are only so many characters in this show!


Ivy, Rufus, and Serena’s Dad

In the most unhinged and unnecessary plotline that is the saga of of Ivy Dickens aka Charlie, the actor-turned-grifter hired to scheme her way into the Van Der Woodsen fortune, Ivy dates both Rufus and Serena’s dad, William. It’s a major ick factor especially because she at one point has a crush on Nate, and at another point has a hot chef boyfriend in L.A. she could have easily stayed with. She’s obsessed with Lily’s sloppy seconds!


Blair, Marcus, and Catherine

In what may be the most obtuse of all the bananas love triangles on this cursed show, Blair starts dating Marcus, a Lord who has a very hot and tough to deal with step-mother, Catherine, whom Blair tries incessantly to please. Blair blackmails Catherine after she catches her hooking up with Nate — but then Vanessa later catches Marcus hooking up with Catherine — yikes!


Thanks for reading,
head home for more!